1 /* $OpenBSD: tlslegacytest.c,v 1.7 2022/10/02 16:39:39 jsing Exp $ */ 2 /* 3 * Copyright (c) 2015, 2016, 2017, 2020 Joel Sing <jsing@openbsd.org> 4 * 5 * Permission to use, copy, modify, and distribute this software for any 6 * purpose with or without fee is hereby granted, provided that the above 7 * copyright notice and this permission notice appear in all copies. 8 * 9 * THE SOFTWARE IS PROVIDED "AS IS" AND THE AUTHOR DISCLAIMS ALL WARRANTIES 10 * WITH REGARD TO THIS SOFTWARE INCLUDING ALL IMPLIED WARRANTIES OF 11 * MERCHANTABILITY AND FITNESS. IN NO EVENT SHALL THE AUTHOR BE LIABLE FOR 12 * ANY SPECIAL, DIRECT, INDIRECT, OR CONSEQUENTIAL DAMAGES OR ANY DAMAGES 13 * WHATSOEVER RESULTING FROM LOSS OF USE, DATA OR PROFITS, WHETHER IN AN 14 * ACTION OF CONTRACT, NEGLIGENCE OR OTHER TORTIOUS ACTION, ARISING OUT OF 15 * OR IN CONNECTION WITH THE USE OR PERFORMANCE OF THIS SOFTWARE. 16 */ 17 18 #include <openssl/ssl.h> 19 20 #include <err.h> 21 #include <stdio.h> 22 #include <string.h> 23 24 /* openssl.org:443 */ 25 static uint8_t tls12_server_response[] = { 26 0x16, 0x03, 0x03, 0x00, 0x3d, 0x02, 0x00, 0x00, 27 0x39, 0x03, 0x03, 0x62, 0x0c, 0x8a, 0x7e, 0x29, 28 0x60, 0xcb, 0x08, 0xd1, 0xb4, 0x95, 0x68, 0x76, 29 0xea, 0x4e, 0x0c, 0x94, 0xf2, 0x42, 0x3d, 0xd1, 30 0x7a, 0xc2, 0xfe, 0x6c, 0xb3, 0xe6, 0x12, 0x8a, 31 0x33, 0x02, 0x92, 0x00, 0xc0, 0x30, 0x00, 0x00, 32 0x11, 0xff, 0x01, 0x00, 0x01, 0x00, 0x00, 0x0b, 33 0x00, 0x04, 0x03, 0x00, 0x01, 0x02, 0x00, 0x23, 34 0x00, 0x00, 35 }; 36 37 /* 38 * outlook.office365.com:587 with starttls - this server response includes 39 * multiple handshake messages contained in a single TLS record. 40 */ 41 static uint8_t tls12_server_response_with_cert[] = { 42 0x16, 0x03, 0x03, 0x0f, 0x2b, 0x02, 0x00, 0x00, 43 0x4d, 0x03, 0x03, 0x5f, 0x7c, 0x69, 0x42, 0xe1, 44 0x19, 0xf0, 0x22, 0xfb, 0x71, 0x9a, 0xf1, 0x63, 45 0x34, 0xbb, 0x61, 0x46, 0xea, 0x5f, 0x0b, 0x5e, 46 0xb1, 0x4e, 0x37, 0x96, 0x67, 0xff, 0x83, 0xea, 47 0x0e, 0x16, 0x85, 0x20, 0x3a, 0x1b, 0x00, 0x00, 48 0x17, 0xe9, 0xac, 0xca, 0x19, 0x61, 0xaf, 0x70, 49 0x28, 0x3b, 0x18, 0xaa, 0x6c, 0xa0, 0x0f, 0x78, 50 0xd0, 0x83, 0xfc, 0x5d, 0x78, 0xf9, 0x6d, 0xdb, 51 0x16, 0x21, 0x15, 0xa2, 0xc0, 0x30, 0x00, 0x00, 52 0x05, 0xff, 0x01, 0x00, 0x01, 0x00, 0x0b, 0x00, 53 0x0d, 0x47, 0x00, 0x0d, 0x44, 0x00, 0x08, 0xaf, 54 0x30, 0x82, 0x08, 0xab, 0x30, 0x82, 0x07, 0x93, 55 0xa0, 0x03, 0x02, 0x01, 0x02, 0x02, 0x0c, 0x6d, 56 0xea, 0x0b, 0xe1, 0x97, 0x27, 0x60, 0xa1, 0x59, 57 0xb1, 0x85, 0x60, 0x30, 0x0d, 0x06, 0x09, 0x2a, 58 0x86, 0x48, 0x86, 0xf7, 0x0d, 0x01, 0x01, 0x0b, 59 0x05, 0x00, 0x30, 0x66, 0x31, 0x0b, 0x30, 0x09, 60 0x06, 0x03, 0x55, 0x04, 0x06, 0x13, 0x02, 0x42, 61 0x45, 0x31, 0x19, 0x30, 0x17, 0x06, 0x03, 0x55, 62 0x04, 0x0a, 0x13, 0x10, 0x47, 0x6c, 0x6f, 0x62, 63 0x61, 0x6c, 0x53, 0x69, 0x67, 0x6e, 0x20, 0x6e, 64 0x76, 0x2d, 0x73, 0x61, 0x31, 0x3c, 0x30, 0x3a, 65 0x06, 0x03, 0x55, 0x04, 0x03, 0x13, 0x33, 0x47, 66 0x6c, 0x6f, 0x62, 0x61, 0x6c, 0x53, 0x69, 0x67, 67 0x6e, 0x20, 0x4f, 0x72, 0x67, 0x61, 0x6e, 0x69, 68 0x7a, 0x61, 0x74, 0x69, 0x6f, 0x6e, 0x20, 0x56, 69 0x61, 0x6c, 0x69, 0x64, 0x61, 0x74, 0x69, 0x6f, 70 0x6e, 0x20, 0x43, 0x41, 0x20, 0x2d, 0x20, 0x53, 71 0x48, 0x41, 0x32, 0x35, 0x36, 0x20, 0x2d, 0x20, 72 0x47, 0x33, 0x30, 0x1e, 0x17, 0x0d, 0x32, 0x30, 73 0x30, 0x38, 0x31, 0x33, 0x32, 0x33, 0x31, 0x38, 74 0x34, 0x39, 0x5a, 0x17, 0x0d, 0x32, 0x32, 0x30, 75 0x38, 0x31, 0x34, 0x32, 0x33, 0x31, 0x38, 0x34, 76 0x39, 0x5a, 0x30, 0x6a, 0x31, 0x0b, 0x30, 0x09, 77 0x06, 0x03, 0x55, 0x04, 0x06, 0x13, 0x02, 0x55, 78 0x53, 0x31, 0x13, 0x30, 0x11, 0x06, 0x03, 0x55, 79 0x04, 0x08, 0x13, 0x0a, 0x57, 0x61, 0x73, 0x68, 80 0x69, 0x6e, 0x67, 0x74, 0x6f, 0x6e, 0x31, 0x10, 81 0x30, 0x0e, 0x06, 0x03, 0x55, 0x04, 0x07, 0x13, 82 0x07, 0x52, 0x65, 0x64, 0x6d, 0x6f, 0x6e, 0x64, 83 0x31, 0x1e, 0x30, 0x1c, 0x06, 0x03, 0x55, 0x04, 84 0x0a, 0x13, 0x15, 0x4d, 0x69, 0x63, 0x72, 0x6f, 85 0x73, 0x6f, 0x66, 0x74, 0x20, 0x43, 0x6f, 0x72, 86 0x70, 0x6f, 0x72, 0x61, 0x74, 0x69, 0x6f, 0x6e, 87 0x31, 0x14, 0x30, 0x12, 0x06, 0x03, 0x55, 0x04, 88 0x03, 0x13, 0x0b, 0x6f, 0x75, 0x74, 0x6c, 0x6f, 89 0x6f, 0x6b, 0x2e, 0x63, 0x6f, 0x6d, 0x30, 0x82, 90 0x01, 0x22, 0x30, 0x0d, 0x06, 0x09, 0x2a, 0x86, 91 0x48, 0x86, 0xf7, 0x0d, 0x01, 0x01, 0x01, 0x05, 92 0x00, 0x03, 0x82, 0x01, 0x0f, 0x00, 0x30, 0x82, 93 0x01, 0x0a, 0x02, 0x82, 0x01, 0x01, 0x00, 0xc9, 94 0x20, 0x3f, 0x57, 0xb9, 0xf9, 0x71, 0xaa, 0x3c, 95 0x6a, 0x0a, 0x5d, 0x3f, 0xc9, 0x8d, 0x99, 0xa5, 96 0x50, 0x26, 0x25, 0x4e, 0xdc, 0x69, 0x52, 0xb3, 97 0x33, 0x70, 0xe7, 0x72, 0xa2, 0x83, 0x92, 0x54, 98 0xd1, 0xd4, 0x86, 0x15, 0xf2, 0xc4, 0x65, 0xf8, 99 0xbc, 0xe5, 0xd2, 0x1e, 0x12, 0x25, 0x9e, 0x75, 100 0x8e, 0x77, 0xd2, 0x8e, 0x94, 0xca, 0x03, 0x4b, 101 0xf4, 0xc8, 0xca, 0xe3, 0xe3, 0x9b, 0x66, 0xa3, 102 0xa1, 0x37, 0x74, 0xcc, 0xfe, 0xc4, 0x1e, 0x64, 103 0xdc, 0xe3, 0x18, 0xba, 0xc1, 0x7b, 0x39, 0x5b, 104 0xb1, 0x47, 0xe9, 0x11, 0x92, 0xef, 0xee, 0xe6, 105 0x08, 0xcd, 0x93, 0x7b, 0x09, 0xc7, 0x39, 0xfe, 106 0xe5, 0xe2, 0x47, 0x3f, 0x68, 0x78, 0xa4, 0x17, 107 0x78, 0x13, 0xcb, 0x12, 0x38, 0x9d, 0x89, 0x2b, 108 0x1f, 0x75, 0x9b, 0x87, 0x5d, 0x53, 0xfc, 0xb0, 109 0x2a, 0xaf, 0x2d, 0x86, 0x8a, 0x76, 0x3b, 0xce, 110 0x5e, 0xae, 0x43, 0x74, 0x68, 0xc3, 0x28, 0xbf, 111 0x10, 0x2f, 0xdd, 0xd9, 0x43, 0x4b, 0x2d, 0xa6, 112 0xdc, 0x1f, 0x6d, 0x90, 0xd0, 0xce, 0x14, 0x1e, 113 0x6c, 0xdc, 0x7b, 0x06, 0xe4, 0x7b, 0xa9, 0x81, 114 0x40, 0xed, 0xde, 0x18, 0xb7, 0xdf, 0x53, 0x61, 115 0xbc, 0x18, 0x83, 0x11, 0xc7, 0xb4, 0x1b, 0x99, 116 0xef, 0x14, 0xe4, 0x63, 0x39, 0xe3, 0x5c, 0x2f, 117 0xe7, 0x89, 0x58, 0x5b, 0xda, 0x03, 0x3a, 0x39, 118 0x96, 0x8a, 0xca, 0x4f, 0xd8, 0xe3, 0x6c, 0x7f, 119 0x6e, 0xd3, 0xe7, 0x30, 0x34, 0x9c, 0xdb, 0x8b, 120 0xe8, 0x6a, 0xa6, 0x08, 0x77, 0x1d, 0x63, 0xd6, 121 0x57, 0x9d, 0xcd, 0xa7, 0x47, 0x05, 0x39, 0x96, 122 0x7b, 0xfd, 0x9a, 0x09, 0x99, 0xef, 0x49, 0xb1, 123 0x89, 0x02, 0xbe, 0x4f, 0xb8, 0xef, 0xa0, 0x04, 124 0x29, 0x74, 0xfb, 0x9a, 0x7e, 0x9d, 0xa8, 0x10, 125 0xfb, 0x7e, 0xb0, 0x6c, 0x60, 0x4f, 0x57, 0x02, 126 0x03, 0x01, 0x00, 0x01, 0xa3, 0x82, 0x05, 0x53, 127 0x30, 0x82, 0x05, 0x4f, 0x30, 0x0e, 0x06, 0x03, 128 0x55, 0x1d, 0x0f, 0x01, 0x01, 0xff, 0x04, 0x04, 129 0x03, 0x02, 0x05, 0xa0, 0x30, 0x81, 0x9e, 0x06, 130 0x08, 0x2b, 0x06, 0x01, 0x05, 0x05, 0x07, 0x01, 131 0x01, 0x04, 0x81, 0x91, 0x30, 0x81, 0x8e, 0x30, 132 0x4b, 0x06, 0x08, 0x2b, 0x06, 0x01, 0x05, 0x05, 133 0x07, 0x30, 0x02, 0x86, 0x3f, 0x68, 0x74, 0x74, 134 0x70, 0x3a, 0x2f, 0x2f, 0x73, 0x65, 0x63, 0x75, 135 0x72, 0x65, 0x2e, 0x67, 0x6c, 0x6f, 0x62, 0x61, 136 0x6c, 0x73, 0x69, 0x67, 0x6e, 0x2e, 0x63, 0x6f, 137 0x6d, 0x2f, 0x63, 0x61, 0x63, 0x65, 0x72, 0x74, 138 0x2f, 0x67, 0x73, 0x6f, 0x72, 0x67, 0x61, 0x6e, 139 0x69, 0x7a, 0x61, 0x74, 0x69, 0x6f, 0x6e, 0x76, 140 0x61, 0x6c, 0x73, 0x68, 0x61, 0x32, 0x67, 0x33, 141 0x2e, 0x63, 0x72, 0x74, 0x30, 0x3f, 0x06, 0x08, 142 0x2b, 0x06, 0x01, 0x05, 0x05, 0x07, 0x30, 0x01, 143 0x86, 0x33, 0x68, 0x74, 0x74, 0x70, 0x3a, 0x2f, 144 0x2f, 0x6f, 0x63, 0x73, 0x70, 0x32, 0x2e, 0x67, 145 0x6c, 0x6f, 0x62, 0x61, 0x6c, 0x73, 0x69, 0x67, 146 0x6e, 0x2e, 0x63, 0x6f, 0x6d, 0x2f, 0x67, 0x73, 147 0x6f, 0x72, 0x67, 0x61, 0x6e, 0x69, 0x7a, 0x61, 148 0x74, 0x69, 0x6f, 0x6e, 0x76, 0x61, 0x6c, 0x73, 149 0x68, 0x61, 0x32, 0x67, 0x33, 0x30, 0x56, 0x06, 150 0x03, 0x55, 0x1d, 0x20, 0x04, 0x4f, 0x30, 0x4d, 151 0x30, 0x41, 0x06, 0x09, 0x2b, 0x06, 0x01, 0x04, 152 0x01, 0xa0, 0x32, 0x01, 0x14, 0x30, 0x34, 0x30, 153 0x32, 0x06, 0x08, 0x2b, 0x06, 0x01, 0x05, 0x05, 154 0x07, 0x02, 0x01, 0x16, 0x26, 0x68, 0x74, 0x74, 155 0x70, 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0x4d, 0x46, 0x10, 0xe8, 0x20, 0xed, 0x7b, 502 0xcd, 0x73, 0xed, 0x03, 0x6a, 0x4c, 0x49, 0xaf, 503 0xbe, 0xa3, 0xe0, 0xab, 0x9a, 0xb8, 0xf8, 0x06, 504 0x25, 0x31, 0x8d, 0x32, 0x44, 0xfd, 0xd6, 0xb0, 505 0xd4, 0x6c, 0x9a, 0x2a, 0x0f, 0xab, 0xe2, 0x13, 506 0x10, 0x6d, 0x41, 0x0b, 0x97, 0x74, 0xa0, 0x04, 507 0x16, 0x60, 0xf1, 0x8e, 0x74, 0xf3, 0x91, 0x75, 508 0x2b, 0x92, 0x2b, 0xc7, 0x5b, 0x6f, 0x1d, 0x70, 509 0xe2, 0xc6, 0x9a, 0x7d, 0x66, 0x55, 0x98, 0x01, 510 0x71, 0xb8, 0xdd, 0xf4, 0x70, 0xc9, 0x74, 0x56, 511 0xcc, 0xa5, 0x2c, 0x51, 0x70, 0x72, 0xc2, 0x44, 512 0xb9, 0x59, 0xc3, 0xc3, 0xf8, 0x29, 0x4e, 0x79, 513 0x40, 0x9b, 0x30, 0x35, 0x66, 0xb2, 0xd8, 0x7d, 514 0xfe, 0x65, 0x6b, 0xf0, 0x17, 0xa3, 0x13, 0xc7, 515 0xc7, 0xc6, 0x48, 0xb2, 0xae, 0x4f, 0x26, 0x0b, 516 0x8a, 0x40, 0xaa, 0x06, 0x65, 0x8a, 0x95, 0x00, 517 0xc4, 0xc9, 0xfd, 0x69, 0x0a, 0xa9, 0x0a, 0x18, 518 0xff, 0x95, 0x40, 0xab, 0x84, 0x75, 0xfe, 0x11, 519 0xb1, 0x6f, 0xca, 0x5e, 0xf7, 0xe4, 0x1d, 0x8d, 520 0x08, 0x1c, 0xd3, 0x95, 0xf4, 0x9b, 0x17, 0x41, 521 0xa8, 0x8f, 0x6e, 0xfa, 0x6c, 0x43, 0x60, 0x39, 522 0x0a, 0xa2, 0x7e, 0xdf, 0x3e, 0x74, 0xc2, 0xbf, 523 0xaf, 0x96, 0x96, 0xbd, 0x21, 0x4b, 0x0d, 0x00, 524 0x00, 0x1a, 0x03, 0x01, 0x02, 0x40, 0x00, 0x12, 525 0x04, 0x01, 0x05, 0x01, 0x02, 0x01, 0x04, 0x03, 526 0x05, 0x03, 0x02, 0x03, 0x02, 0x02, 0x06, 0x01, 527 0x06, 0x03, 0x00, 0x00, 0x0e, 0x00, 0x00, 0x00, 528 }; 529 530 struct tlslegacy_client_test { 531 const unsigned char *desc; 532 unsigned char *server_response; 533 const size_t server_response_len; 534 const SSL_METHOD *(*ssl_method)(void); 535 int want_state; 536 }; 537 538 static struct tlslegacy_client_test tlslegacy_client_tests[] = { 539 { 540 .desc = "TLSv1.2 legacy fallback", 541 .server_response = tls12_server_response, 542 .server_response_len = sizeof(tls12_server_response), 543 .ssl_method = TLS_client_method, 544 .want_state = SSL3_ST_CR_CERT_A, 545 }, 546 { 547 .desc = "TLSv1.2 legacy fallback with server cert", 548 .server_response = tls12_server_response_with_cert, 549 .server_response_len = sizeof(tls12_server_response_with_cert), 550 .ssl_method = TLS_client_method, 551 .want_state = SSL3_ST_CR_KEY_EXCH_B, 552 }, 553 }; 554 555 #define N_TLSLEGACY_CLIENT_TESTS \ 556 (sizeof(tlslegacy_client_tests) / sizeof(*tlslegacy_client_tests)) 557 558 static int 559 tlslegacy_client_test(int testno, struct tlslegacy_client_test *tct) 560 { 561 BIO *rbio = NULL, *wbio = NULL; 562 SSL_CTX *ssl_ctx = NULL; 563 SSL *ssl = NULL; 564 int ret = 1; 565 566 fprintf(stderr, "Test %d - %s\n", testno, tct->desc); 567 568 if ((rbio = BIO_new_mem_buf(tct->server_response, 569 tct->server_response_len)) == NULL) { 570 fprintf(stderr, "Failed to setup rbio\n"); 571 goto failure; 572 } 573 if ((wbio = BIO_new(BIO_s_mem())) == NULL) { 574 fprintf(stderr, "Failed to setup wbio\n"); 575 goto failure; 576 } 577 578 if ((ssl_ctx = SSL_CTX_new(tct->ssl_method())) == NULL) { 579 fprintf(stderr, "SSL_CTX_new() returned NULL\n"); 580 goto failure; 581 } 582 583 if ((ssl = SSL_new(ssl_ctx)) == NULL) { 584 fprintf(stderr, "SSL_new() returned NULL\n"); 585 goto failure; 586 } 587 588 BIO_up_ref(rbio); 589 BIO_up_ref(wbio); 590 SSL_set_bio(ssl, rbio, wbio); 591 592 if (SSL_connect(ssl) == 1) { 593 fprintf(stderr, "SSL_connect() succeeded\n"); 594 goto failure; 595 } 596 597 if (SSL_state(ssl) != tct->want_state) { 598 fprintf(stderr, "FAIL: Got SSL state %x, want %x", 599 SSL_state(ssl), tct->want_state); 600 goto failure; 601 } 602 603 ret = 0; 604 605 failure: 606 SSL_CTX_free(ssl_ctx); 607 SSL_free(ssl); 608 609 BIO_free(rbio); 610 BIO_free(wbio); 611 612 return (ret); 613 } 614 615 int 616 main(int argc, char **argv) 617 { 618 int failed = 0; 619 size_t i; 620 621 for (i = 0; i < N_TLSLEGACY_CLIENT_TESTS; i++) 622 failed |= tlslegacy_client_test(i, &tlslegacy_client_tests[i]); 623 624 return (failed); 625 } 626